The title compound, C13H12O8·0.5H2O, has two molecules of 3,4,5-triacetoxybenzoic acid and one of water in the asymmetric unit. These are linked by intermolecular hydrogen bonds to form a larger unit, which is composed of four molecules of the acid and two molecules of water.
Supporting information
CCDC reference: 640511
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.055
- wR factor = 0.173
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact O8 .. C14 .. 2.84 Ang.
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C1 .. 5.23 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for O9 - C14 .. 5.23 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C9
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.
5-Carboxybenzene-1,2,3-triyl triacetate hemihydrate
top
Crystal data top
C13H12O8·0.5H2O | Z = 4 |
Mr = 305.24 | F(000) = 636 |
Triclinic, P1 | Dx = 1.314 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4384 (18) Å | Cell parameters from 1659 reflections |
b = 9.797 (2) Å | θ = 2.3–22.1° |
c = 19.276 (4) Å | µ = 0.11 mm−1 |
α = 83.705 (4)° | T = 294 K |
β = 81.735 (4)° | Prism, colorless |
γ = 78.980 (4)° | 0.22 × 0.20 × 0.16 mm |
V = 1542.4 (6) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5397 independent reflections |
Radiation source: fine-focus sealed tube | 2633 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick,1996) | h = −7→10 |
Tmin = 0.971, Tmax = 0.984 | k = −11→11 |
8005 measured reflections | l = −22→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: geom, difmap for H2O |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0718P)2 + 0.5172P] where P = (Fo2 + 2Fc2)/3 |
5397 reflections | (Δ/σ)max < 0.001 |
389 parameters | Δρmax = 0.39 e Å−3 |
42 restraints | Δρmin = −0.19 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.6844 (5) | 0.4509 (5) | 0.4504 (2) | 0.0576 (10) | |
C2 | 0.7726 (4) | 0.3702 (4) | 0.50722 (18) | 0.0458 (9) | |
C3 | 0.7899 (4) | 0.2254 (4) | 0.51472 (19) | 0.0515 (10) | |
H3 | 0.7426 | 0.1795 | 0.4856 | 0.062* | |
C4 | 0.8772 (4) | 0.1513 (3) | 0.56542 (19) | 0.0481 (9) | |
C5 | 0.9535 (4) | 0.2161 (4) | 0.60784 (18) | 0.0471 (9) | |
C6 | 0.9344 (4) | 0.3609 (4) | 0.60049 (18) | 0.0463 (9) | |
C7 | 0.8426 (4) | 0.4371 (4) | 0.55099 (18) | 0.0471 (9) | |
H7 | 0.8278 | 0.5341 | 0.5471 | 0.056* | |
C8 | 0.7875 (6) | −0.0546 (4) | 0.6161 (2) | 0.0683 (12) | |
C9 | 0.8200 (7) | −0.2075 (4) | 0.6117 (3) | 0.1088 (18) | |
H9A | 0.8161 | −0.2271 | 0.5643 | 0.163* | |
H9B | 0.7391 | −0.2484 | 0.6428 | 0.163* | |
H9C | 0.9258 | −0.2460 | 0.6250 | 0.163* | |
C10 | 1.1896 (5) | 0.0604 (4) | 0.6350 (3) | 0.0652 (11) | |
C11 | 1.2604 (6) | −0.0258 (5) | 0.6951 (3) | 0.1014 (17) | |
H11A | 1.3585 | −0.0863 | 0.6779 | 0.152* | |
H11B | 1.1837 | −0.0810 | 0.7194 | 0.152* | |
H11C | 1.2850 | 0.0340 | 0.7268 | 0.152* | |
C12 | 0.9510 (5) | 0.4351 (4) | 0.7100 (2) | 0.0572 (11) | |
C13 | 1.0469 (6) | 0.5030 (5) | 0.7504 (2) | 0.0891 (15) | |
H13A | 1.1415 | 0.4377 | 0.7620 | 0.134* | |
H13B | 0.9813 | 0.5328 | 0.7928 | 0.134* | |
H13C | 1.0799 | 0.5824 | 0.7224 | 0.134* | |
C14 | 0.5072 (5) | 0.5351 (5) | 0.7588 (2) | 0.0659 (12) | |
C15 | 0.5689 (4) | 0.5953 (4) | 0.81504 (19) | 0.0526 (10) | |
C16 | 0.6035 (4) | 0.5126 (4) | 0.87630 (19) | 0.0522 (10) | |
H16 | 0.5887 | 0.4202 | 0.8822 | 0.063* | |
C17 | 0.6597 (4) | 0.5693 (4) | 0.92759 (19) | 0.0494 (9) | |
C18 | 0.6792 (4) | 0.7070 (4) | 0.9202 (2) | 0.0534 (10) | |
C19 | 0.6462 (5) | 0.7878 (4) | 0.8590 (2) | 0.0548 (10) | |
C20 | 0.5909 (4) | 0.7333 (4) | 0.8065 (2) | 0.0585 (11) | |
H20 | 0.5684 | 0.7883 | 0.7654 | 0.070* | |
C21 | 0.8238 (6) | 0.3969 (6) | 0.9927 (3) | 0.0839 (15) | |
C22 | 0.8333 (6) | 0.3206 (6) | 1.0631 (3) | 0.110 (2) | |
H22A | 0.9230 | 0.2437 | 1.0604 | 0.166* | |
H22B | 0.7339 | 0.2859 | 1.0786 | 0.166* | |
H22C | 0.8490 | 0.3825 | 1.0958 | 0.166* | |
C23 | 0.6274 (6) | 0.8116 (4) | 1.0259 (2) | 0.0703 (12) | |
C24 | 0.7093 (6) | 0.8634 (6) | 1.0787 (3) | 0.1097 (18) | |
H24A | 0.6347 | 0.8789 | 1.1208 | 0.165* | |
H24B | 0.7437 | 0.9493 | 1.0599 | 0.165* | |
H24C | 0.8024 | 0.7952 | 1.0895 | 0.165* | |
C25 | 0.8111 (7) | 0.9567 (5) | 0.8286 (2) | 0.0811 (14) | |
C26 | 0.8110 (7) | 1.1074 (5) | 0.8290 (3) | 0.1125 (19) | |
H26A | 0.9207 | 1.1242 | 0.8191 | 0.169* | |
H26B | 0.7641 | 1.1376 | 0.8743 | 0.169* | |
H26C | 0.7481 | 1.1583 | 0.7936 | 0.169* | |
O1 | 0.6498 (3) | 0.5830 (3) | 0.45316 (14) | 0.0781 (9) | |
H1 | 0.6138 | 0.6195 | 0.4169 | 0.094* | |
O2 | 0.6521 (4) | 0.3884 (4) | 0.40333 (17) | 0.0953 (11) | |
O3 | 0.8995 (3) | 0.0053 (2) | 0.57227 (14) | 0.0619 (7) | |
O4 | 0.6793 (4) | 0.0106 (3) | 0.65244 (18) | 0.0917 (11) | |
O5 | 1.0413 (3) | 0.1398 (3) | 0.65892 (13) | 0.0612 (7) | |
O6 | 1.2453 (4) | 0.0668 (3) | 0.57464 (19) | 0.0888 (10) | |
O7 | 1.0140 (3) | 0.4283 (3) | 0.64134 (13) | 0.0584 (7) | |
O8 | 0.8320 (4) | 0.3886 (3) | 0.73337 (16) | 0.0869 (10) | |
O9 | 0.5043 (4) | 0.6132 (4) | 0.70012 (17) | 0.0972 (11) | |
H9 | 0.4718 | 0.5736 | 0.6710 | 0.146* | |
O10 | 0.4625 (4) | 0.4214 (4) | 0.76968 (16) | 0.0847 (10) | |
O11 | 0.6881 (3) | 0.4917 (3) | 0.99127 (13) | 0.0604 (7) | |
O12 | 0.9208 (5) | 0.3792 (5) | 0.9415 (2) | 0.1340 (15) | |
O13 | 0.7405 (3) | 0.7623 (3) | 0.97190 (14) | 0.0633 (8) | |
O14 | 0.4868 (4) | 0.8112 (4) | 1.02703 (18) | 0.0959 (11) | |
O15 | 0.6614 (4) | 0.9276 (3) | 0.85329 (15) | 0.0713 (8) | |
O16 | 0.9204 (5) | 0.8691 (4) | 0.8106 (2) | 0.1120 (13) | |
O17 | 0.5511 (4) | 0.7321 (3) | 0.33873 (15) | 0.0831 (9) | |
H17B | 0.5399 | 0.6839 | 0.3055 | 0.100* | |
H17A | 0.4692 | 0.7959 | 0.3496 | 0.100* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.058 (3) | 0.061 (3) | 0.050 (3) | −0.005 (2) | −0.001 (2) | −0.006 (2) |
C2 | 0.049 (2) | 0.045 (2) | 0.041 (2) | −0.0052 (17) | −0.0035 (18) | −0.0052 (17) |
C3 | 0.059 (2) | 0.051 (2) | 0.047 (2) | −0.0129 (19) | −0.002 (2) | −0.0120 (19) |
C4 | 0.059 (2) | 0.031 (2) | 0.051 (2) | −0.0056 (17) | 0.004 (2) | −0.0080 (18) |
C5 | 0.053 (2) | 0.044 (2) | 0.040 (2) | −0.0036 (18) | −0.0014 (18) | −0.0008 (18) |
C6 | 0.053 (2) | 0.043 (2) | 0.044 (2) | −0.0116 (18) | −0.0037 (19) | −0.0062 (18) |
C7 | 0.053 (2) | 0.037 (2) | 0.048 (2) | −0.0051 (17) | −0.0008 (19) | −0.0029 (18) |
C8 | 0.083 (3) | 0.036 (2) | 0.080 (3) | −0.013 (2) | 0.012 (3) | 0.000 (2) |
C9 | 0.124 (4) | 0.053 (3) | 0.135 (4) | −0.016 (3) | 0.032 (3) | −0.008 (3) |
C10 | 0.059 (3) | 0.054 (3) | 0.081 (3) | −0.008 (2) | −0.009 (3) | −0.003 (2) |
C11 | 0.081 (4) | 0.084 (3) | 0.127 (5) | 0.006 (3) | −0.026 (3) | 0.025 (3) |
C12 | 0.061 (3) | 0.055 (3) | 0.052 (3) | 0.000 (2) | −0.004 (2) | −0.012 (2) |
C13 | 0.092 (4) | 0.115 (4) | 0.071 (3) | −0.019 (3) | −0.027 (3) | −0.029 (3) |
C14 | 0.056 (3) | 0.086 (3) | 0.054 (3) | −0.013 (2) | −0.009 (2) | 0.003 (3) |
C15 | 0.043 (2) | 0.066 (3) | 0.047 (2) | −0.0029 (19) | −0.0085 (18) | −0.006 (2) |
C16 | 0.047 (2) | 0.058 (2) | 0.050 (2) | −0.0085 (18) | −0.0025 (19) | −0.002 (2) |
C17 | 0.040 (2) | 0.059 (3) | 0.043 (2) | 0.0013 (18) | −0.0028 (18) | 0.001 (2) |
C18 | 0.047 (2) | 0.064 (3) | 0.047 (2) | −0.0006 (19) | −0.0010 (19) | −0.014 (2) |
C19 | 0.052 (2) | 0.050 (2) | 0.058 (3) | −0.0004 (19) | 0.000 (2) | −0.006 (2) |
C20 | 0.054 (3) | 0.062 (3) | 0.052 (3) | 0.005 (2) | −0.009 (2) | 0.005 (2) |
C21 | 0.057 (3) | 0.120 (4) | 0.058 (3) | 0.011 (3) | −0.003 (2) | 0.008 (3) |
C22 | 0.084 (4) | 0.144 (5) | 0.079 (4) | 0.014 (3) | −0.016 (3) | 0.040 (3) |
C23 | 0.073 (3) | 0.070 (3) | 0.066 (3) | 0.001 (2) | −0.009 (2) | −0.021 (2) |
C24 | 0.114 (4) | 0.128 (4) | 0.093 (3) | −0.004 (3) | −0.026 (3) | −0.049 (3) |
C25 | 0.094 (4) | 0.058 (3) | 0.081 (3) | −0.012 (3) | 0.018 (3) | −0.001 (3) |
C26 | 0.126 (4) | 0.084 (3) | 0.120 (4) | −0.029 (3) | 0.021 (3) | −0.007 (3) |
O1 | 0.082 (2) | 0.076 (2) | 0.0617 (19) | 0.0098 (16) | −0.0088 (15) | 0.0128 (16) |
O2 | 0.106 (3) | 0.118 (3) | 0.067 (2) | −0.007 (2) | −0.0361 (19) | −0.017 (2) |
O3 | 0.0749 (19) | 0.0360 (15) | 0.0701 (18) | −0.0105 (13) | 0.0109 (15) | −0.0092 (13) |
O4 | 0.090 (2) | 0.0489 (18) | 0.117 (3) | −0.0043 (16) | 0.038 (2) | −0.0083 (18) |
O5 | 0.0614 (18) | 0.0593 (17) | 0.0537 (16) | 0.0085 (14) | −0.0072 (14) | 0.0023 (13) |
O6 | 0.070 (2) | 0.101 (3) | 0.088 (2) | −0.0018 (18) | 0.0066 (19) | −0.019 (2) |
O7 | 0.0668 (18) | 0.0607 (17) | 0.0528 (17) | −0.0222 (14) | −0.0065 (14) | −0.0096 (13) |
O8 | 0.081 (2) | 0.109 (3) | 0.074 (2) | −0.027 (2) | 0.0165 (18) | −0.0325 (19) |
O9 | 0.110 (2) | 0.124 (3) | 0.068 (2) | −0.031 (2) | −0.0371 (19) | 0.001 (2) |
O10 | 0.085 (2) | 0.113 (3) | 0.069 (2) | −0.045 (2) | −0.0098 (17) | −0.0122 (19) |
O11 | 0.0499 (16) | 0.0749 (18) | 0.0485 (16) | 0.0025 (14) | −0.0040 (13) | 0.0018 (14) |
O12 | 0.094 (3) | 0.177 (3) | 0.087 (2) | 0.054 (2) | 0.005 (2) | 0.024 (2) |
O13 | 0.0548 (17) | 0.0800 (19) | 0.0554 (17) | −0.0057 (14) | −0.0040 (14) | −0.0218 (15) |
O14 | 0.065 (2) | 0.129 (3) | 0.093 (3) | −0.004 (2) | 0.0064 (19) | −0.050 (2) |
O15 | 0.078 (2) | 0.0537 (19) | 0.075 (2) | −0.0022 (15) | 0.0026 (16) | −0.0065 (15) |
O16 | 0.091 (2) | 0.081 (2) | 0.151 (3) | −0.0149 (19) | 0.024 (2) | 0.000 (2) |
O17 | 0.105 (2) | 0.0561 (18) | 0.083 (2) | 0.0094 (16) | −0.0226 (18) | −0.0143 (16) |
Geometric parameters (Å, º) top
C1—O2 | 1.236 (5) | C14—C15 | 1.488 (6) |
C1—O1 | 1.276 (5) | C15—C20 | 1.389 (5) |
C1—C2 | 1.484 (5) | C15—C16 | 1.391 (5) |
C2—C7 | 1.380 (5) | C16—C17 | 1.366 (5) |
C2—C3 | 1.392 (5) | C16—H16 | 0.9300 |
C3—C4 | 1.368 (5) | C17—C18 | 1.379 (5) |
C3—H3 | 0.9300 | C17—O11 | 1.397 (4) |
C4—C5 | 1.381 (5) | C18—C19 | 1.379 (5) |
C4—O3 | 1.401 (4) | C18—O13 | 1.388 (4) |
C5—O5 | 1.384 (4) | C19—C20 | 1.371 (5) |
C5—C6 | 1.390 (5) | C19—O15 | 1.391 (4) |
C6—C7 | 1.380 (5) | C20—H20 | 0.9300 |
C6—O7 | 1.394 (4) | C21—O12 | 1.195 (5) |
C7—H7 | 0.9300 | C21—O11 | 1.332 (5) |
C8—O4 | 1.193 (5) | C21—C22 | 1.480 (6) |
C8—O3 | 1.351 (5) | C22—H22A | 0.9600 |
C8—C9 | 1.480 (6) | C22—H22B | 0.9600 |
C9—H9A | 0.9600 | C22—H22C | 0.9600 |
C9—H9B | 0.9600 | C23—O14 | 1.184 (5) |
C9—H9C | 0.9600 | C23—O13 | 1.370 (5) |
C10—O6 | 1.190 (5) | C23—C24 | 1.491 (6) |
C10—O5 | 1.387 (5) | C24—H24A | 0.9600 |
C10—C11 | 1.485 (6) | C24—H24B | 0.9600 |
C11—H11A | 0.9600 | C24—H24C | 0.9600 |
C11—H11B | 0.9600 | C25—O16 | 1.174 (5) |
C11—H11C | 0.9600 | C25—O15 | 1.356 (5) |
C12—O8 | 1.191 (5) | C25—C26 | 1.476 (6) |
C12—O7 | 1.358 (4) | C26—H26A | 0.9600 |
C12—C13 | 1.484 (6) | C26—H26B | 0.9600 |
C13—H13A | 0.9600 | C26—H26C | 0.9600 |
C13—H13B | 0.9600 | O1—H1 | 0.8200 |
C13—H13C | 0.9600 | O9—H9 | 0.8200 |
C14—O10 | 1.231 (5) | O17—H17B | 0.8621 |
C14—O9 | 1.294 (5) | O17—H17A | 0.8567 |
| | | |
O2—C1—O1 | 124.4 (4) | C16—C15—C14 | 119.6 (4) |
O2—C1—C2 | 119.1 (4) | C17—C16—C15 | 118.9 (4) |
O1—C1—C2 | 116.4 (4) | C17—C16—H16 | 120.5 |
C7—C2—C3 | 119.8 (3) | C15—C16—H16 | 120.5 |
C7—C2—C1 | 120.5 (3) | C16—C17—C18 | 121.3 (4) |
C3—C2—C1 | 119.6 (3) | C16—C17—O11 | 120.6 (4) |
C4—C3—C2 | 119.2 (3) | C18—C17—O11 | 118.0 (3) |
C4—C3—H3 | 120.4 | C19—C18—C17 | 119.4 (4) |
C2—C3—H3 | 120.4 | C19—C18—O13 | 119.8 (4) |
C3—C4—C5 | 121.7 (3) | C17—C18—O13 | 120.7 (4) |
C3—C4—O3 | 119.9 (3) | C20—C19—C18 | 120.6 (4) |
C5—C4—O3 | 118.3 (3) | C20—C19—O15 | 120.6 (4) |
C4—C5—O5 | 121.0 (3) | C18—C19—O15 | 118.7 (4) |
C4—C5—C6 | 118.7 (3) | C19—C20—C15 | 119.5 (4) |
O5—C5—C6 | 120.2 (3) | C19—C20—H20 | 120.3 |
C7—C6—C5 | 120.2 (3) | C15—C20—H20 | 120.3 |
C7—C6—O7 | 120.1 (3) | O12—C21—O11 | 121.3 (4) |
C5—C6—O7 | 119.7 (3) | O12—C21—C22 | 126.9 (5) |
C2—C7—C6 | 120.3 (3) | O11—C21—C22 | 111.7 (4) |
C2—C7—H7 | 119.9 | C21—C22—H22A | 109.5 |
C6—C7—H7 | 119.9 | C21—C22—H22B | 109.5 |
O4—C8—O3 | 122.8 (4) | H22A—C22—H22B | 109.5 |
O4—C8—C9 | 126.7 (4) | C21—C22—H22C | 109.5 |
O3—C8—C9 | 110.5 (4) | H22A—C22—H22C | 109.5 |
C8—C9—H9A | 109.5 | H22B—C22—H22C | 109.5 |
C8—C9—H9B | 109.5 | O14—C23—O13 | 122.2 (4) |
H9A—C9—H9B | 109.5 | O14—C23—C24 | 128.0 (4) |
C8—C9—H9C | 109.5 | O13—C23—C24 | 109.8 (4) |
H9A—C9—H9C | 109.5 | C23—C24—H24A | 109.5 |
H9B—C9—H9C | 109.5 | C23—C24—H24B | 109.5 |
O6—C10—O5 | 122.1 (4) | H24A—C24—H24B | 109.5 |
O6—C10—C11 | 128.3 (4) | C23—C24—H24C | 109.5 |
O5—C10—C11 | 109.6 (4) | H24A—C24—H24C | 109.5 |
C10—C11—H11A | 109.5 | H24B—C24—H24C | 109.5 |
C10—C11—H11B | 109.5 | O16—C25—O15 | 121.6 (4) |
H11A—C11—H11B | 109.5 | O16—C25—C26 | 127.9 (5) |
C10—C11—H11C | 109.5 | O15—C25—C26 | 110.4 (4) |
H11A—C11—H11C | 109.5 | C25—C26—H26A | 109.5 |
H11B—C11—H11C | 109.5 | C25—C26—H26B | 109.5 |
O8—C12—O7 | 121.5 (4) | H26A—C26—H26B | 109.5 |
O8—C12—C13 | 125.7 (4) | C25—C26—H26C | 109.5 |
O7—C12—C13 | 112.8 (4) | H26A—C26—H26C | 109.5 |
C12—C13—H13A | 109.5 | H26B—C26—H26C | 109.5 |
C12—C13—H13B | 109.5 | C1—O1—H1 | 109.5 |
H13A—C13—H13B | 109.5 | C8—O3—C4 | 117.5 (3) |
C12—C13—H13C | 109.5 | C5—O5—C10 | 116.2 (3) |
H13A—C13—H13C | 109.5 | C12—O7—C6 | 116.3 (3) |
H13B—C13—H13C | 109.5 | C14—O9—H9 | 109.5 |
O10—C14—O9 | 125.0 (4) | C21—O11—C17 | 118.3 (3) |
O10—C14—C15 | 120.9 (4) | C23—O13—C18 | 115.2 (3) |
O9—C14—C15 | 114.1 (4) | C25—O15—C19 | 116.5 (3) |
C20—C15—C16 | 120.3 (4) | H17B—O17—H17A | 114.6 |
C20—C15—C14 | 120.1 (4) | | |
| | | |
O2—C1—C2—C7 | 165.3 (4) | C17—C18—C19—C20 | 1.5 (5) |
O1—C1—C2—C7 | −13.3 (5) | O13—C18—C19—C20 | 177.7 (3) |
O2—C1—C2—C3 | −12.4 (5) | C17—C18—C19—O15 | 178.0 (3) |
O1—C1—C2—C3 | 169.0 (3) | O13—C18—C19—O15 | −5.8 (5) |
C7—C2—C3—C4 | −0.4 (5) | C18—C19—C20—C15 | −0.3 (6) |
C1—C2—C3—C4 | 177.3 (3) | O15—C19—C20—C15 | −176.7 (3) |
C2—C3—C4—C5 | −2.2 (5) | C16—C15—C20—C19 | −0.4 (5) |
C2—C3—C4—O3 | −178.2 (3) | C14—C15—C20—C19 | 179.3 (3) |
C3—C4—C5—O5 | 180.0 (3) | O4—C8—O3—C4 | −5.7 (6) |
O3—C4—C5—O5 | −4.0 (5) | C9—C8—O3—C4 | 174.3 (4) |
C3—C4—C5—C6 | 2.8 (5) | C3—C4—O3—C8 | −90.2 (4) |
O3—C4—C5—C6 | 178.8 (3) | C5—C4—O3—C8 | 93.7 (4) |
C4—C5—C6—C7 | −0.8 (5) | C4—C5—O5—C10 | 72.5 (4) |
O5—C5—C6—C7 | −178.0 (3) | C6—C5—O5—C10 | −110.4 (4) |
C4—C5—C6—O7 | −178.2 (3) | O6—C10—O5—C5 | 6.5 (6) |
O5—C5—C6—O7 | 4.6 (5) | C11—C10—O5—C5 | −174.2 (3) |
C3—C2—C7—C6 | 2.3 (5) | O8—C12—O7—C6 | −1.7 (5) |
C1—C2—C7—C6 | −175.3 (3) | C13—C12—O7—C6 | 177.5 (3) |
C5—C6—C7—C2 | −1.7 (5) | C7—C6—O7—C12 | 107.8 (4) |
O7—C6—C7—C2 | 175.6 (3) | C5—C6—O7—C12 | −74.8 (4) |
O10—C14—C15—C20 | −168.4 (4) | O12—C21—O11—C17 | 1.1 (7) |
O9—C14—C15—C20 | 10.9 (5) | C22—C21—O11—C17 | −178.1 (4) |
O10—C14—C15—C16 | 11.4 (6) | C16—C17—O11—C21 | 78.2 (5) |
O9—C14—C15—C16 | −169.4 (4) | C18—C17—O11—C21 | −106.2 (4) |
C20—C15—C16—C17 | −0.1 (5) | O14—C23—O13—C18 | −2.4 (6) |
C14—C15—C16—C17 | −179.9 (3) | C24—C23—O13—C18 | 178.1 (4) |
C15—C16—C17—C18 | 1.4 (5) | C19—C18—O13—C23 | 97.8 (4) |
C15—C16—C17—O11 | 176.8 (3) | C17—C18—O13—C23 | −86.0 (4) |
C16—C17—C18—C19 | −2.1 (5) | O16—C25—O15—C19 | 2.9 (7) |
O11—C17—C18—C19 | −177.6 (3) | C26—C25—O15—C19 | −177.0 (4) |
C16—C17—C18—O13 | −178.3 (3) | C20—C19—O15—C25 | −96.0 (5) |
O11—C17—C18—O13 | 6.2 (5) | C18—C19—O15—C25 | 87.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O17 | 0.82 | 1.85 | 2.655 (4) | 168 |
O9—H9···O2i | 0.82 | 1.86 | 2.548 (4) | 141 |
O17—H17B···O10i | 0.86 | 1.87 | 2.733 (4) | 174 |
O17—H17A···O4i | 0.86 | 2.06 | 2.879 (4) | 159 |
Symmetry code: (i) −x+1, −y+1, −z+1. |